(2Z)-3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one

• ChemBase ID: 120229
• Molecular Formular: C16H13F6N5O
• Molecular Mass: 405.2977392
• Monoisotopic Mass: 405.10242938
• SMILES: c1(n2c(nn1)CN(C(=O)/C=C(/Cc1c(cc(c(c1)F)F)F)\N)CC2)C(F)(F)F
• Canonical SMILES: N/C(=C\C(=O)N1CCn2c(C1)nnc2C(F)(F)F)/Cc1cc(F)c(cc1F)F
• InChI: InChI=1S/C16H13F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4-6H,1-3,7,23H2/b9-5-
• InChIKey: RLSFDUAUKXKPCZ-UITAMQMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one
• IUPAC Traditional name: (2Z)-3-amino-1-[3-(trifluoromethyl)-5H,6H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one
• Synonyms: (Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one; (2Z)-3-Amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-2-buten-1-one; 2,3-Desdihydrogen rac-Sitagliptin; (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine; (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine

Database IDs

• CAS Number: 767340-03-4
• PubChem SID: 162214582
• PubChem CID: 29986152

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.1287907
• LogD (pH = 7.4): 1.1287973
• Log P: 1.1287974
• Molar Refractivity: 89.1187 cm^3
• Polarizability: 30.88889 Å^3
• Polar Surface Area: 77.04 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 19.409695

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - O865000

Sitagliptin intermediate. A dipeptidyl peptidase-4 inhibitor and an anti-hypertensive agent for the treatment of diabetes and hypertension.

REFERENCES

• Kim, D., et al.: J. Med. Chem., 48, 141 (2005)
• Ahren, B., et al.: Eur. J. Pharmacol., 521 164 (2005)
• Bergman, A., et al: Clin. Ther., 28, 55 (2006)